Mike,
27k Ouch. You could get a nearly new 90/110 for that kind of money. My SII SWB is in excellent condition (chassis bulkhead solid with no rust at all, well apart from the door tops) and cost less than $5000. Its first run was 800 miles and it never missed a beat. Driven sensibly these things really are reliable; you've just got to look after it.
OK to the questions:
I wanted to know from you guys with a 109 how do they drive? I drive a 88" and that's far better than I expected. I believe that the 109" is better ride wise.
Are there drums all around? Yes - but they do do the job, just make sure your hub seals aren't leaking.
Power steering? No - but there was a thread running in here where someone was going to try and fit it. I don't know how far they got.
Is the clutch a workout to use? Yes and no - Compared to a modern family car, yes; compared to an old F350, no.
I use to have an old beatup 79 F-350 with a 4 on the floor and I loved driving it so would it be comparable to driving something like that? I think it would. If you want the kind of vehicle where you want to listen to the sounds the trucks make rather than some cd or radio; smell the oils and lubes; have to check the oil each and every time you get in; get a feel for the temp so you know how much choke you'll need; be prapared to dedicate some serious time to keeping it in top order then a Seires is the wagon for you.
Do you actualy need the high performance engine? Mine is a stock 3 bearing 2.25 (with a webber carb) and while it is not a flying machine it certainly keeps up with day to day traffic. On the Motorway (Highway) it will sit at 60 mph all day and will do 70 if I wanted to thrash it.
Is there nowhere you can get a 25 year old Series in good condition and then export that. The money you save will allow you to do exactly what you want to it. Remember most of that 27k is going to be eaten up in labour charges and there is nothing too difficult on the SIII and the parts are not expensive; just look here:
http://www.paddockspares.com/main.asp?category=SERIES
Hope the blurb above helps.
Dave